Ethanol → Ethyl 2-(2,6-difluorophenyl)thiazole-4-carboxylate

HRID 73599Notes

Reaction equation

HRID 73599 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4](=[S:6])[NH2:5].C([CH:14](Br)[C:15](=O)[C:16]([O-:18])=[O:17])C.[CH2:21](O)[CH3:22]>>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]1[S:6][CH:14]=[C:15]([C:16]([O:18][CH2:21][CH3:22])=[O:17])[N:5]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 126832122,6-Difluorobenzene-1-carbothioamideHCID 21948992Ethylbromopyruvate

Product 1

HCID 59455697Ethyl 2-(2,6-difluorophenyl)thiazole-4-carboxylateYield 84%

Procedure

A solution of 2,6-difluorobenzothioamide (1.0 eq) and ethylbromopyruvate (1.0 eq.) in ethanol (1.0 M) was heated in the microwave at 130° C. for 30 minutes. Upon removal of volatiles in vacuo, ethyl acetate was added and the solution was washed with Na2CO3(sat.), with NaCl(sat.), was dried over MgSO4, filtered and concentrated yielding ethyl 2-(2,6-difluorophenyl)thiazole-4-carboxylate (84%). LCMS (m/z): 270.1 (MH+); LC Rt=3.79 min.

Workup

  1. customUpon removal of volatiles in vacuo, ethyl acetate
  2. additionwas added
  3. washthe solution was washed with Na2CO3(sat.), with NaCl(sat.)
  4. dry with materialwas dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-36e5daa9d98c4f339d3cd7bf710c73a9
Source dataset
uspto-grants-2014_09
Patent number
US08829193B2

Reaction notes

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